The present invention relates to a new group of compounds having protected hydroxy groups which are precursors for organoleptic compounds, such as fragrances and masking agents and antimicrobial compounds.
A principal strategy currently employed in imparting odors to consumer products is admixing a fragrance directly into the product. There are, however, several drawbacks to this strategy. The fragrance material can be too volatile, resulting in undesired fragrance loss during manufacturing, storage, and use. Many fragrance materials also are unstable over time. This, again, results in undesired fragrance loss during storage.
In many consumer products, it is desirable for the fragrance to be released slowly over time. Microencapsulation and inclusion complexes with cyclodextrins have been used to help decrease volatility, improve stability and provide slow-release properties. However, these methods are, for a number of reasons, often not successful. In addition, cyclodextrins are too expensive to use commercially.
Fragrance precursors for scenting fabrics which are washed in the presence of lipase-containing detergents are described in WO 95/04809. The fragrance precursors contained in the detergent and/or in the softener are cleaved by the lipase and a single odoriferous compound, either an odoriferous alcohol or aldehyde or ketone, is yielded. Thereby, a prolonged scenting effect on the fabric is reportedly obtained.
In summary, the methods and compositions set forth above suffer from various drawbacks which make them less desirable for use as long lasting, e.g., organoleptic and/or antimicrobial compounds.
Accordingly, one object of the present invention is to provide new compounds which are precursors having different activities.
It is another object of the present invention to provide compounds that are cleaved under different activating conditions.
A further object of the invention is to provide new compounds which are stable under transport and storage conditions.
A further object of the present invention is to provide a precursor molecule that supplies different active compounds simultaneously or successively.
These and other objects of the present invention will become apparent from the present disclosure and claims.
The present invention relates to compounds of formula (I): 
wherein Y is 
m is an integer of 1 or greater;
n is 1, 2or 3;
R1, R2, R3, R4, R5 and R6 represent independently hydrogen, substituted or unsubstituted alkyl-, alkenyl-, alkinyl-, cycloalkyl-, cycloalkenyl- or aromatic radicals which can additionally contain one or more 
whereby one or two rings can be built by the combination of the respective R1 to R6 groups and these ring(s) can be substituted with one or more alkyl group;
X is xe2x80x94OR7 and R7 is the residue of an alcohol R7OH, or the residue of the enol form of an aldehyde or ketone, or X is a primary or secondary amino group forming an amide;
Z is 
q is the same or greater than m;
R8 is hydrogen, a straight or branched, unsubstituted or substituted alkyl-, alkenyl-, cycloalkyl-, cycloalkenyl- or aromatic radical which optionally includes and/or is substituted with one or more heteroatoms, and/or group(s) including a heteroatom, preferably by xe2x80x94COxe2x80x94, OCOR7, COOR7, COY, Si and/or N;
R9 is the residue xe2x80x94OR12 of an alcohol of formula R12 OH or the residue of the enol form of an aldehyde or ketone or has the definition given for Y and R9 where Y can be the same or different and optionally includes and/or is substituted with a heteroatom, and/or group(s) including a heteroatom;
R10 and R11 represent independently hydrogen, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or an aromatic residue which optionally includes and/or is substituted with one or more heteroatoms, and/or group(s) containing a heteroatom.
Another embodiment is a composition including a compound of formula (I) as a precursor for at least one organoleptic compound.
Another embodiment is a laundry composition including a compound of formula (I) which forms an organoleptic compound and/or a fluorescent coumarin when activated.
Another embodiment is a compound of formula (I), wherein Y is
m is an integer of 1 or greater
n is 1, 2, or 3;
R1, R2, R3, R4, R5 and R6 represent independently hydrogen, substituted or unsubstituted alkyl-, alkenyl-, alkinyl-, cycloaklyl-, cycloalkenyl- or aromatic radicals which can additionally contain one or more xe2x80x94Oxe2x80x94 and/or xe2x80x94Cxe2x80x94 groups;
whereby one or two rings can be built by the combination of the respective R1 to R6 and the ring(s) can be substituted by one or more alkyl groups;
X is xe2x80x94OR7 and R7 is the residue of an alcohol R7OH having 6 or more carbon atoms, or the residue of the enol form of an aldehyde having 6 or more carbon atoms or the residue of the enol form of a ketone having 7 or more carbon atoms;
Z is 
q is the same or bigger than m;
R8 represents hydrogen, a straight or branched, unsubstituted or substituted alkyl-, alkenyl-, cycloalkyl-, cycloalkenyl- or aromatic radical which optionally includes and/or is substituted by one or more heteroatoms, and/or group(s) including a heretoatom;
R9 is the residue xe2x80x94OR12 of an alcohol of formula R12OH or the residue of the enol form of an aldehyde or ketone or has the definition given for Y and R9 and Y can be the same or different and optionally includes and/or is substituted by a heteroatom and/or group(s) including a heteroatom;
R10 and R11 represent independently hydrogen, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or an aromatic residue which optionally include and/or are substituted by one or more heteroatoms and/or group(s) including a heteroatom.
The compounds of formula (I) are not limited to any particular stereoisomers. Thus, all possible stereoisomers (E/Z isomers, enantiomers, diastereomers) and all mixtures thereof are included within the scope of the present invention.
The compounds of formula (I) are virtually odorless under room temperature, atmospheric conditions and about 20 to 100% relative humidity. However, under activating conditions, they are cleaved and one or more active compounds with organoleptic and/or antimicrobial properties are generated.
As used herein, the phrases xe2x80x9cactivating conditionsxe2x80x9d or xe2x80x9cactivatedxe2x80x9d are used interchangeably and are intended to mean those conditions which lead to cleavage of the compounds of formula (I) and the formation of xe2x80x9cactive,xe2x80x9d i.e., organoleptic and/or antimicrobial agents. For example, the following activating conditions lead to cleavage of compounds of formula (I) and to formation of the desired active compounds: skin bacteria, especially axilla bacteria; enzymes such as protease or lipase; elevated temperature; acidic or alkaline pH-values; and/or light.
The compounds of formula (I), upon cleavage, form lactones and optionally aldehydes, ketones, and/or alcohols having organoleptic and/or antimicrobial activity. Thus, the compounds of formula (I) permit the development of useful consumer products with enhanced organoleptic and/or microbiological properties. Further, the compounds of formula (I), upon cleavage can generate fluorescent coumarins useful as optical brighteners.
The compounds of formula (I) of the present invention are cleaved under activating conditions in two successive steps. First the xe2x80x9cprotective groupxe2x80x9d Z is removed resulting in a hydroxyester according to the following reaction: 
The hydroxyester (II) decomposes into one or more organoleptic lactone(s), and one or more alcohol(s), amine(s), aldehyde(s) and/or ketone(s). 
In the present invention, Z is a protective group which prevents the hydroxy ester Yxe2x80x94H (II) from premature cyclisation to an organoleptic lactone (III). At the same time, Z can generate one or more additional organoleptic compound(s).
In the following reaction, cleavage of a xcex2-ketoester of formula (I) is shown. 
wherein,
1 is Zxe2x80x94Y, a protected hydroxy ester (xcex2-ketoester);
2 is ZH, a hydroxyester;
3 is an organoleptic lactone;
4 is an organoleptic alcohol;
5 is an xcex2-ketoacid; and
6 is an organoleptic ketone.
Thus, one compound of formula (I) can be cleaved to form, under activating conditions, three different organoleptic compounds.
When Z is 
it is the residue of an odorless or antimicrobial acid optionally substituted by groups yielding, upon cleavage, one or more organoleptic compounds. Examples of esters in which R8 is an odorless acid are:
tetradecanoic acid 1-(2-hex-3-enyloxycarbonyl-ethyl)-heptyl ester;
tetradecanoic acid 1-[2-(3,7-dimethyl-octa-2,6-dienyloxycarbonyl)-ethyl]-octyl ester;
benzoic acid 1-[2-(3,7-dimethyl-octa-2,6-dienyloxycarbonyl)-ethyl]-octyl ester;
dodecanoic acid 1-[2-(3,7-dimethyl-oct-6-enyloxycarbonyl)-ethyl]-heptyl ester;
succinic acid 1-[2-(1,5-dimethyl-1-vinyl-hex-4-enyloxycarbonyl)-ethyl]-heptyl ester hex-3-enyl ester is a compound wherein R8 is COR7;
succinic acid bis-{1-[2-(3,7-dimethyl-octa-2,6-dienyloxycarbonyl)-ethyl]-octyl} ester with R8 being COY.
When Z is 
R9 is preferably the residue of an organoleptic compound or Y as defined previously. Examples of carbonates in which R9 is an organoleptic compound are:
4-phenethyloxycarbonyloxy-decanoic acid 3,7-dimethyl-oct-6-enyl-ester;
4-phenethyloxycarbonyloxy-decanoic acid hex-3-enyl ester;
4-hex-3-enyloxycarbonyloxy-undecanoic acid 3,7-dimethyl-octa-2,6-dienyl ester;
4-phenethyloxycarbonyloxy-undecanoic acid 3,7-dimethyl-octa-2,6-dienyl ester;
4-{1-[2-(1,1,5-trimethyl-hexyloxycarbonyl)-ethyl]octyloxycarbonyloxy}-decanoic acid 1,1,5-trimethyl-hexyl ester is a carbonate with R9 being Y.
When Z is 
is preferably derived from a non odorous mono- or diamine. The compound 4-(Bis-decyl-carbamoyloxy)-undecanoic acid hex-3-enyl ester is an example of a preferred carbamate.
In the present invention, formula (I):
can also be a photolabile ester.
The compounds of the present invention may be employed as fragrance precursors in a variety of compositions, including, for example, personal care products, laundry products, cleaning compositions, pet care products and environment scents such as air fresheners.
The compounds of the present invention may also be employed as precursors for odor masking agents, e.g. in the same products as the fragrance precursors.
The compounds of the present invention also may be employed as precursors for antimicrobial agents.
When the compounds of the present invention are employed as fragrance precursors and precursors for odor masking agents, they are present in such compositions individually in an amount effective to enhance or to mask the characteristic odor of a material. More commonly, however, the compounds are mixed with other fragrance components in an amount sufficient to provide the desired odor characteristics.
In the present invention, due to the in situ generation of the active compounds, the desired effect is prolonged and the substantivity on different substrates is enhanced. If two or more active compounds are provided, they can be generated, depending on the precursor and/or the activating conditions, simultaneously or successively. Further, the compounds of the invention provide slow release of the active agents.
A broad range of known odorants or odorant mixtures can be generated from compounds of the invention.
Non-limiting examples of aldehydes generated from the compounds of the present invention include:
2,6,10-trimethylundec-9-enal*;
1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-napthalenecar-boxaldehyde;
tridecanal;
2-[4-(1-methylethyl)phenyl]-ethanal;
2,4-dimethyl-cyclohex-3-ene-1-carbox-aldehyde*;
4-carboxaldehyde-1,3,5-trimethyl-cyclohex-1-ene*;
1-carboxaldehyde-2,4-dimethyl-cyclohex-3-ene*;
1-carboxaldehyde-4-(4-hydroxy-4-methylpentyl)-cyclohex-3-ene*;
3,5,5-trimethyl-hexanal;
heptanal*;
2,6-dimethyl-hept-5-enal*;
decanal**;
dec-9-enal;
dec-4-enal;
2-methyldecanal*;
undec-10-enal**;
undecanal*;
dodecanal**;
2-methyl-undecanal**;
octanal**;
nonanal*;
3,5,5-trimethylhexanal;
undec-9-enal**;
2-phenyl-propanal*;
4-methyl-phenyl-acetaldehyde*;
3,7-dimethyl-octanal*;
dihydrofarnesal**;
7-hydroxy-3,7-dimethyl-octanal*;
2,6-dimethyl-oct-5-enal;
2-[4-(1-methylethyl)phenyl]-ethanal*;
3-(3-isopropyl-phenyl)-butanal**;
2-(3,7-dimethyoct-6-enoxy)-ethanal;
1-carboxaldehyde-4-(4-methyl-3-pentenyl)-cyclohex-3-ene*;
2,3,5,5-tetramethyl-hexanal;
longifolic aldehyde;
2-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)-butanal*;
2-methyl-3-(4-tert-butylphenyl)-propanal**;
4-(1,1-dimethyl-ethyl)-benzene-propanal*;
2-[4-(1-methylethyl)-phenyl]-propanal;
alpha-methyl-1,3-benzodioxole-5-propanal*;
3,7-dimethyl-oct-6-enal*;
2-methyl-3-(4-isopropylphenyl)-propionaldehyde*;
4-(4-hydroxy-4-methyl-pentyl)-cyclohex-3-en-1-carboxaldehyde**;
alpha-methyl-,1,3-benzodioxole-5-propanal*;
1-carboxaldehyde-4-(1,1-dimethylethyl)-cyclohexane;
4-(octahydro-4,7-methano-5H-inden-5-ylidene)-butanal;
[(3,7-dimethyl-6-octenyl)-oxy]-acetaidehyde**;
hex-2-enal*;
2-nonenal*;
2-tridecenal*;
3,7-dimethyl-oct-2,6-dien-1-al*;
2-nonadienal*;
2,4-dimethyl-2,6-heptadienal;
trans-dec-2-en-1-al*
2,4-diethyl-hep-2,6-dien-1-al*
dodec-2-en-1-al*
3,7-dimethyl-oct-2,6-dien-1-al*
2,4-diethyl-hepta-2,6-dienal;
3,7-dimethyl-nona-2,6-dien-1-al*
3-propyl-2-hepten-1-al; and
1-carboxaldehyde-4-(prop-2-en-2-yl)-cyclohex-1-ene.
In the list above, one asterisk (*) indicates preferred aldehydes and two asterisks (**) indicate more preferred aldehydes.
Non-limiting examples of ketones generated from the compounds of the present invention include:
2-heptyl-cyclopentanone;
2,2,6,10-tetrametyltricyclo-[5.4.0.0(6,10)]-undecan-4-one benzylacetone*;
carvone*;
1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamentyl-4H-inden-4-one*;
methyl heptenone*;
dimethyl octenone*;
2,5-dimethyl-oct-2-en-6-one**;
2-(butan-2-yl)-cyclohexanone*;
2-hexyl-cyclopent-2-en-1-one*;
2-(1-methylethyl)-5-methyl-cyclohexanone*;
2-(2-methylethyl)-5-methyl-cyclohexanone**;
3-methyl-cyclopentadecanone;
4-(1,1-dimethylpropyl)pentyl-cyclohexanone*;
4-tert-pentyl-cyclohexanone*;
2-oxo-1-pentyl-cyclopentane-acetic acid methyl ester**;
3-oxo-2-pentyl-cyclopentane-acetic acid methyl ester**;
1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-ethanone*;
3-methyl-5-propyl-cyclohex-2-en-1-one*;
4-(2,6,6-trimethylcyclohex-1-en-1-yl)butan-2-one**;
4-(2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-one**;
2-methyl-5-(1-methylethenyl)-cyclohex-2-en-1-one*;
cyclopentadecanone**;
1-(4-hydroxyphenyl)-butan-3-one**;
4-benzo-1,3-dioxo-5-yl-but-2-one**;
4-(1,3-benzodioxol-5-yl)-2-butanone**;
nonan-3-one*;
nonan-2-one*;
octan-2-one*;
2-heptanone*;
butan-2-one*;
6-methyl-hept-5-en-2-one*;
6,10-dimethyl-undeca-5,9-dien-2-one*;
1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one*;
1-(2-cyclohexen)-2,4,4-trimethyl-but-2-enone*;
carvone**;
2-hexyl-cyclo-pent-2-en-1-one**;
2-pentyl-cyclopent-2-en-1-one;
3-methyl-2-pentyl-cyclopent-2-en-1-one**;
2-hexylidenecyclopentanone*;
3,5-diethyl-5,6-dimethyl-2-cyclohexenone*;
4,4A,5,6,7,8-hexahydro-6-isopropenyl-4,4A-dimethyl-2(3H)napthalenone**;
3-methyl-6-propylidenecyclohexanone*;
4-(1-methylethyl)-cyclohex-2-en-1-one;
(E)-oct-3-en-2-one;
1-(2,3,4,7,8,8A-hexahydro-3,6,8,8-tetramethyl-1H-3A,7-methanoazulen-5-yl)-ethanone*;
2-hydroxy-3,5-dimethyl-cyclopent-2-ene-1-one*;
1-(3,3-dimethyl-1-cyclohexen-1-yl)ethanone*;
1-(2,4,6-trimethylcyclohex-3-en-1-yl)-but-1-en-3-one;
acetylisolongifolene;
2-(3-methylbut-2-en-1-yl)-3-methyl-cyclopent-2-en-1-one;
2,6,6-trimethyl-1,3-cyclohexadienyl-1-carbaldehyde**;
3-methyl-5-(2,2,3-trimethylcyclopent-3-ene-1-yl)pent-3-ene-2-one*;
5-butylidene-2,2,4-trimethylcyclopentanone;
1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4H-inden-4-one**;
3-methyl-5-propyl-cyclohex-2-en-1-one**;
4,4A,5,6,7,8-hexahydro-6-isopropyl-2(3H)-naphthalenone;
4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-butan-2-one**;
4-methoxyphenylethanone**;
acetophenone*;
1-(2-naphthalenyl)-ethanone**;
3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one**;
2-acetylpyrazine*;
3,5,5-trimethyl-cyclohex-2-en-1,4-dione*;
(E)-5-methyl-2-hepten-4-one;
acetyl diisoamylene**;
dec-3-en-2-one;
2-ethyl-3,6,6-trimethylcyclohex-2-enyl-but-2-en-1-one;
1-(5,5-dimethyl-1(6)-cyclohexen-1-yl)-4-penten-1-one**;
1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-but-2-ene-1-one**;
1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-but-2-ene-1-one**;
1-(2,6,6,trimethyl-3-cyclohexen-1-yl)-but-2-ene-1-one**; and
2,4,4,5,5-pentamethyl-1-cyclopentene-1-yl-ethanone*.
In the list above, one asterisk (*) indicates preferred ketones and two asterisks (**) indicates more preferred ketones.
Non-limiting examples of alcohols generated from the compounds of the present invention include primary, secondary and tertiary alcohols and phenols such as:
amyl alcohol;
hexyl alcohol*;
2-hexyl alcohol*;
heptyl alcohol*;
octyl alcohol*;
nonyl alcohol*;
decyl alcohol*;
undecyl alcohol*;
lauryl alcohol*;
myristic alcohol;
3-methyl-but-2-en-1-ol*;
3-methyl-1-pentanol;
cis-3-hexenol*;
cis-4-hexenol*;
3,5,5-trimethyl-hexanol;
3,4,5,6,6-pentamethylheptan-2-ol*;
citronellol*;
geraniol*;
oct-1-en-3-ol;
2,5,7-trimethyl-octan-3-ol;
2-cis-3,7-dimethyl-2,6-octadien-1-ol;
6-ethyl-3-methyl-5-octen-1-ol*;
3,7-dimethyl-oct-3,6-dienol*;
3,7-dimethylectariol*;
7-methoxy-3,7-dimethyl-octan-2-ol*;
cis-6-nonenol*;
5-ethyl-2-nonanol;
6,8-dimethyl-2-nonanol*;
2,2,8-trimethyl-7(8)-nonene-3-ol;
nona-2,6-dien-1-ol;
4-methyl-3-decen-5-ol*;
dec-9-en-1-ol;
benzylalcohol;
2-methyl-undecanol;
10-undecen-1-ol;
1-phenyl-ethanol*;
2-phenyl-ethanol*;
2-methyl-3-phenyl-3-propenol;
2-phenyl-propanol*;
3-phenyl-propanol*;
4-phenyl-2-butanol;
2-methyl-5-phenyl-pentanol*;
2-methyl-4-phenyl-pentanol*;
3-methyl-5-phenyl-pentanol*;
2-(2-methylphenyl)-ethanol*;
4-(1-methylethyl)-benzene-methanol;
4-(4-hydroxyphenyl)-butan-2-one*;
2-phenoxy-ethanol*;
4-(1-methylethyl)-2-hydroxy-1-methyl benzene;
2-methoxy-4-methyl-phenol;
4-methyl-phenol;
anisic alcohol*;
p-tolyl alcohol*;
cinnamic alcohol;*
vanillin*;
ethyl vanillin*;
eugenol*;
isoeugenol*;
thymol;
anethol*;
decahydro-2-naphthalenol;
bomeol*;
cedrenol*;
farnesol*;
fenchyl alcohol*;
menthol*;
3,7,11-trimethyl-2,6,10-dodecatrien-1-ol;
alpha ionol*;
tetrahydro ionol*;
2-(1,1-dimethylethyl)cyclohexanol*;
3-(1,1-dimethylethyl)cyclohexanol*;
4-(1,1-dimethylethyl)cyclohexanol*;
4-isopropyl-cyclohexanol;
6,6-dimethyl-bicyclo[3.3.1]hept-2-ene-2-ethanol;
6,6-dimethyl-bicyclo[3.1.1]hept-2-ene-methanol*;
p-menth-8-en-3-ol*;
3,3,5-trimethyl-cyclohexanol;
2,4,6-trimethyl-3-cyclohexenyl-methanol*;
4-(1-methylethyl)-cyclohexyl-methanol*;
4-(1,1-dimethylethyl)-cyclohexanol;
2-(1,1-dimethylethyl)-cyclohexanol;
2,2,6-trimethyl-alpha-propyl-cyclohexane propanol*;
5-(2,2,3-trimethyl-3-cyclopentenyl)-3-methylpentan-2-ol*;
3-methyl-5-(2,2,3-trimethylcyclopentyl-3-enyl)pent-;
4-en-2-ol*;
2-ethyl-4(2,2,3-trimethylcyclopentyl-3-enyl)but-2-en-1-ol*;
4-(5,5,6-trimethylbicyclo[2.2.1]hept-2-yl)-cyclohexanol*;
2-(2-methylpropyl)4-hydroxy-4-methyl-tetrahydropyran*;
2-cyclohexyl-propanol*;
2-(1,1-dimethylethyl)-4-methyl-cyclohexanol*;
1-(2-tert-butyl-cyclohexyloxy)-2-butanol*;
1-(4-isopropyl-cyclohexyl)-ethanol*;
1-(4-hydroxyphenyl)-butan-3-one;
2,6-dimethyl-oct-7-en-2-ol**;
2,6-dimethyl-heptan-2-ol**; and
3,7-dimethyl-octa-1,6-dien-3-ol**.
In the list above, one asterisk (*) indicates preferred alcohols and two asterisks (**) indicate more preferred alcohols.
Examples of lactones generated from the compounds of the present invention include:
6-methyl-pyran-2-one;
5-heptyldihydro-2(3H)-furanone*;
5-pentyldihydro-2(3H)-furanone*;
5-(3-hexenyl)-dihydro-5-methyl-(Z)-2(3H)-furanone;
5-hexyldihydro-5-methyl-2(3H)-furanone;
5-hexyldihydro-2(3H)-furanone*;
5-octyldihydro-2(3H)-furanone;
8-(1-methylethyl)-1-oxaspiro[4.5]-decan-2-one*;
8-methyl-1-oxaspiro[4.5]decan-2-one;
8-ethyl-1-oxaspiro[4.5]decan-2-one;
5-(1,5-dimethyl-4-hexenyl)-dihydro-2(3H)-furanone;
2-oxo-5-butyl-tetrahydrofuran*;
4-methyl-5-pentyl-dihydro-2(3H)-furan-2-one;
5-hexyldihydro-5-methyl-2(3H)-furanone;
dihydro-5-methyl-5-vinyl-2(3H)-furanone;
octahydro-2H-1-benzopyran-2-one;
tetrahydro-6-pentyl-2H-pyran-2-one;
tetrahydro-6-hexyl-2H-pyran-2-one;
tetrahydro-6-heptyl-2H-pyran-2-one;
tetrahydro-6-(3-pentenyl)-(E)-2H-pyran-2-one;
tetrahydro-6-(2-pentenyl)-(Z)-2H-pyran-2-one;
(E)-oxacycloheptadec-10-en-one**;
oxacyclohexadecan-2-one**; and
dodeca-12-olide.
In the list above, one asterisk (*) indicates preferred lactones and two asterisks (**) indicate more preferred lactones.
It is a matter of course, that it is not possible to give a complete list of the organoleptic, especially odoriferous and/or antimicrobial aldehydes, ketones, alcohols and lactones which are generated as a result of the cleavage of the esters of formula (I) by, e.g. skin bacteria, enzymes, elevated temperatures, acidic and/or alkaline pH-values or light. Thus, the lists above are exemplary only and are not intended to limit the scope of the invention in any way.
Manufacturing of compositions containing the compounds of the invention may be-accomplished according to methods known to the perfumer, such as for example, those methods set forth in W. A. Poucher, Perfumes, Cosmetics, Soaps, 2, 7th Edition, Chapman and Hall, London (1974) which is hereby incorporated by reference as if set forth fully again.
The compounds of formula (I) are preferably used as sustained release odorants, to mask or attenuate undesirable odors or to provide additional odors not initially present in consumer products, such as for example, personal care products such as cosmetic products destined for application to human skin such as underarm deodorants or anti-perspirants or other deodorants contacting the body, or in hand lotions, baby powders, baby lotions, ointments, foot products, facial cleansers, body wipes, facial make-up, colognes, after-shave lotions, shaving creams, etc.
Additional compositions which may include compounds of the present invention include, for example laundry detergents, fabric softeners, fabric softener sheets, (automatic) dishwasher detergents, and other enzyme-containing consumer products. Further applications for the present compounds are air fresheners and odorants, odor masking agents and/or antimicrobial agents.
The amount of a compound of the present invention required to produce the desired, overall effect varies depending upon the particular compounds of formula (I) selected, the product in which it will be used, and the particular effect desired.
For example, when a compound of the formula (I) is added either singly or as a mixture to, e.g. a deodorant or laundry product composition at levels ranging from about 0.1% to about 10% by weight, or preferably from about 0.25% to about 4% by weight, an odorant, i.e. an odoriferous, aldehyde, ketone, alcohol or lactone in an xe2x80x9corganoleptically effective amountxe2x80x9d is released when the product is used. This newly formed odorant serves to enhance the odor of the product itself or of a fragrance present in the product.
As used herein, the term xe2x80x9corganoleptically effective amountxe2x80x9d is intended to mean the amount of one or more compounds of the present invention required to achieve the desired effect, e.g. fragrance enhancement and/or odor masking, etc. As set forth above, typically an xe2x80x9corganoleptically effective amountxe2x80x9d is between about 0.1% to about 10% by weight of one or more compounds of the present invention.
Compounds of formula (I) can be prepared by using a wide variety of methods known to the skilled chemist.
For the synthesis of esters see, for example, Comprehensive Organic Chemistry, vol. 2, D. Barton, W. D. Ollis, Pergamon Press, p. 871; for the synthesis of carbonates see Comprehensive Organic Chemistry, vol. 2, D. Barton, W. D. Ollis, Pergamon Press, p. 1070; for the synthesis of carbamates see Comprehensive Organic Chemistry, vol. 2, D. Barton, W. D. Ollis, Pergamon Press, p. 1083. All of these documents are hereby incorporated by reference as if set forth fully again.